Silver-catalyzed regioselective hydroamination of alkenyl diazoacetates to synthesize γ-amino acid equivalents

被引：24
作者：
Ueda, Jun [1 ]
Harada, Shingo [1 ]
Nakayama, Hiroki [1 ]
Nemoto, Tetsuhiro [1 ,2 ]
机构：
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 1-8-1 Inohana, Chiba 2608675, Japan
[2] Chiba Univ, Mol Chiral Res Ctr, Inage Ku, 1-33 Yayoi Cho, Chiba 2638522, Japan
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 25期
关键词：
N-H INSERTION; ASYMMETRIC CONJUGATE ADDITION; CARBENE MIGRATORY INSERTION; FORMAL AMIDE INSERTION; CHIRAL BRONSTED ACID; METAL-CARBENE; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; VINYLOGOUS REACTIVITY; GAMMA(2)-AMINO ACIDS;
D O I：
10.1039/c8ob00894a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple protocol to directly access -amino acid derivatives by intermolecular regioselective hydroamination of trichloroethyl alkenyldiazoacetates with carbamate using a silver tetrafluoroborate catalyst is described. Density functional theory (DFT) calculations to analyze the reaction mechanism revealed that multiple attractive interactions occur in a transition state to promote the vinylogous addition of nitrogen nucleophiles.
引用
收藏
页码：4675 / 4682
页数：8
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